Style & Beauty

60 Of Madonna's Most Iconic Fashion Moments Through The Years

The Queen of Pop truly is a trendsetter like no other.
08/16/2018 05:47am ET | Updated August 20, 2018
HuffPost Illustration/Getty Images

If there’s one person who knows how to express herself, especially when it comes to fashion, it’s Madonna.

Since the 1980s, the Queen of Pop has been pushing the envelope with her style. When she burst onto the scene, she was all about teased hair and lace, which she often paired with rosaries and crosses (a nod to her Catholic upbringing). Then we saw her go through a Marilyn Monroe phase, most notably in her “Material Girl” music video (a nod to the Monroe-starring “Gentlemen Prefer Blondes”). Then came the Blond Ambition era, followed by a slew of other reinventions.

In honor of the Material Girl’s birthday ― she turns 60 on Aug. 16 ― we’re taking a look back at 60 of her most iconic style moments over the years.

From her infamous Jean Paul Gaultier cone bra to her Marie Antoinette–inspired VMAs performance look to her heavenly black gown at this year’s Met Gala, Madonna really has worn it all.

1
1984
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This ensemble, with a lace bustier, tulle skirt and, of course, “boy toy” belt buckle is, hands down, one of Madge’s most memorable looks. She wore it for the first annual MTV Video Music Awards at Radio City Music Hall in New York City.
2
1985
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Eighties-era Madonna loved wearing crosses and rosaries as accessories, as she did at the American Music Awards in 1985.
3
1985
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The singer wore this Versace-esque ensemble during her Virgin tour.
4
1985
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The cross motif made an appearance during Madonna’s Virgin tour. Here she is performing in Minnesota on May 21.
5
1985
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The singer wearing even more cross necklaces and rosaries during the after-party for the closing night of the Virgin tour.
6
1986
Vinnie Zuffante / Getty Images
We’ll never forget the “Italians do it better” T-shirt Madonna wore — a nod to her Italian roots — for her “Papa Don’t Preach” music video, which came out that year.
7
1986
Ron Galella Ltd. / Getty Images
Arriving at a rehearsal for the Lincoln Center Workshop production of “Goose and Tomtom” in New York City, Madonna looked undeniably cool in this white seersucker overcoat and black ensemble.
8
1987
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Madonna wore this bold floral number for a performance.
9
1987
Ron Galella / Getty Images
The “Material Girl” singer channeled Marilyn Monroe for the 14th annual American Music Awards, where she took home a trophy for favorite pop/rock female video artist.
10
1989
Michael Ochs Archives / Getty Images
The star perfectly mixed menswear with lingerie for a sexy yet strong look, like this outfit for a performance in Los Angeles.
11
1989
Michael Ochs Archives / Getty Images
Long before Kim Kardashian and her sisters started rocking bike shorts while out and about, Madonna was wearing them onstage like a total boss. There’s no denying her trendsetting power.
12
1990
Frank Micelotta Archive / Getty Images
Madonna gave the world a true fashion moment when she stepped onstage during her Blond Ambition tour wearing this Jean Paul Gaultier cone bra bodysuit. The bra, which made its runway debut in 1982, was inspired by 1950s bullet bras and the underwear-as-outerwear trend, according to Entertainment Weekly. The outfit garnered plenty of chatter and, of course, will forever be one of her most iconic looks.
13
1990
Frank Micelotta Archive / Getty Images
The Blond Ambition tour was basically a fashion show, featuring a number of other iconic looks, including this flashy, bright fuchsia blazer. And can we just take a moment to appreciate the braid-wrapped high ponytail? The hairstyle is almost as iconic as the cone bra.
14
1990
Frank Micelotta Archive / Getty Images
As we said, the Blond Ambition tour featured a number of memorable looks. With this ensemble, Madonna somehow made a bowler, a cone bra and chunky knee pads a lewk.

15
1990
Frank Micelotta Archive / Getty Images
Here, she rocked a polka dotted outfit, also designed by Gaultier.
16
1990
Kevin.Mazur / INACTIVE / Getty Images
For her performance of “Vogue” at the MTV Video Music Awards, the Queen of Pop channeled original material girl Marie Antoinette.
17
1991
David McGough / Getty Images
The singer (here with Michael Jackson) channeled Monroe once again in a sparkling white gown, oversize furry stole and stunning diamond jewelry from Harry Winston, which she wore to the 69th Academy Awards.
18
1991
Dave Hogan / Getty Images
The performer brought the cone bra back for the 1991 premiere of “Madonna: Truth or Dare” (titled “In Bed With Madonna” outside North America) at the Cannes Film Festival in France. She caused quite a stir with her outfit, which was a pretty loose interpretation of the festival’s formal dress code.
19
1992
Kevin.Mazur / INACTIVE / Getty Images
To celebrate her NSFW book Sex, Madonna (here with its photographer, Steven Meisel) opted for a dirndl, which she paired with a stuffed animal. (Also note her bleached eyebrows.)
20
1993
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This sparkly two-piece outfit was part of the wardrobe for Madonna’s the Girlie Show world tour.
21
1993
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This intricate ensemble was also part of the Girlie Show world tour.
22
1995
Getty Images / Getty Images
Madonna has always been one to push the boundaries with her wardrobe choices. She donned a black latex catsuit, danced in rope and appeared in other bondage gear in her video for “Human Nature,” a true sorry-not-sorry anthem.“The song is about basically saying don’t put me in a box, don’t pin me down, don’t tell me what I can and can’t say. It’s about breaking out of the restraints,” she said of the music video, according to Rolling Stone. “So that’s basically the point of the costume.”
23
1995
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For her performance at the Brit Awards, the star reinvented herself once again and donned a much more angelic ensemble.
24
1995
Time & Life Pictures / Getty Images
For the 12th annual MTV Video Music Awards, Madge went casual cool on the red carpet, pairing a pair of black satin pants with a satin shirt.
25
1996
Steve Granitz / Getty Images
For the premiere of “Evita,” in which Madonna portrays Eva Perón, the singer channeled the former Argentine first lady’s sophisticated style.
26
1997
Ron Galella Ltd. / Getty Images
At the Golden Globes, Madonna (with then-boyfriend Carlos Leon) proved to be the embodiment of the Dolce & Gabbana woman when she arrived wearing this lingerie-inspired dress by the Italian label.
27
1997
Ron Galella / Getty Images
The “Ray of Light” singer went for an intergalactic look for the Gianni Versace–themed Costume Institute Gala at the Metropolitan Museum of Art in New York City.
28
1998
Frank Micelotta Archive / Getty Images
Madonna wore this iconic denim jacket ensemble for her “Ray of Light” music video in 1998. The outfit was one of the more pared down during this period, which marked yet another reinvention for the singer that was quite different from any of her previous phases. As Dazed described it, the album, also called “Ray of Light,” feels “spiritual, elemental, and enlightened.” Around this time, she embraced Kabbala. (On her wrist, you can spot the red string bracelet associated with the religion.)
29
1998
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Madonna (with her brother Christopher Ciccone) at the Vanity Fair Oscar party on March 23 in West Hollywood. She wore a gown by designer Olivier Theyskens, which helped boost his fame in the fashion industry.
30
1998
Kevin.Mazur / INACTIVE / Getty Images
Madge donned another Theyskens creation for the VH1 Fashion Awards. This one was a bold yellow, embellished with hook and eye detailing, which the designer told Vogue was sewn on by hand. The overall aesthetic was very Disney’s Belle–meets–Sally from “The Nightmare Before Christmas.”
31
1998
Jeff Kravitz / Getty Images
Madonna went for another full gown for the Golden Globe Awards. It was definitely a far cry from her cone bra.
32
1998
Jeff Kravitz / Getty Images
For the MTV Video Music Awards in Los Angeles, the singer opted for red snakeskin-effect pants and a long sequined vest.
33
1999
Frank Micelotta Archive / Getty Images
Madonna wore this striking red kimono, another Gaultier creation, for her “Nothing Really Matters” music video. She took the same ensemble to the stage for her performance at that year’s Grammy Awards.
34
2000
KMazur / Getty Images
Britney Spears burst onto the scene in the late ’90s and often cited Madonna as her top inspiration. The “Frozen” singer was a fan of Spears’ and at reportedly became obsessed with wearing Britney T-shirts, thinking they would bring her luck.
35
2000
Stephane Cardinale / Corbis / Getty Images
Madge wore this western-inspired ensemble to the MTV Europe Music Awards in Stockholm.
36
2001
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Madonna made sure everyone knew she was Mrs. Guy Ritchie when she walked the red carpet at the “Snatch” premiere, wearing this bridal-white crystal-encrusted blazer. The singer and director tied the knot in December the previous year.
37
2003
Frank Micelotta / Getty Images
Who can forget this MTV VMAs moment? Madonna swapped spit with Spears and Christina Aguilera in front of the world, and while the quick kisses were definitely the talk of the town, what the women were wearing was just as much a part of the moment.
38
2004
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Madonna gave a nod to her famous “Italians do it better” T-shirt with this “Kabbalists do it better” version.
39
2005
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For her “Confessions on a Dance Floor” phase, which was heavily disco inspired, she favored Farrah Fawcett–style hair and plenty of period dancewear.
40
2005
Dave M. Benett / Getty Images
The singer wore this white tailored outfit for her performance at “Live 8” in London’s Hyde Park on July 2.
41
2006
KMazur / Getty Images
For her performance at the Grammys, Madonna donned a light purple outfit resembling her bodysuit in the “Hung Up” video while echoing her 2003 VMAs ensemble.
42
2007
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Madonna wore this classic black gown, with modern bondage-inspired straps, to the Vanity Fair Oscar party with Ritchie.
43
2009
Kevin Mazur / Getty Images
For “The Model as Muse: Embodying Fashion” Costume Institute Gala, the singer donned this Louis Vuitton ensemble, complete with bunny ears. It’s the same outfit she wore in the label’s fall/winter ad campaign that year.
44
2011
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She took daughter Lourdes Leon with her to the Vanity Fair Oscar party, where the singer opted for the sheer lace number with a black bodysuit underneath.
45
2011
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This starry blue Stella McCartney gown is perhaps one of Madonna’s most conventionally pretty outfits. She wore it for that year’s Met Gala, which honored Alexander McQueen, in New York City.
46
2011
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The star went for another very pretty look for the Venice Film Festival. This gown was by Vionnet.
47
2012
Steve Granitz / Getty Images
Madonna wearing a Reem Acra dress at the 69th Annual Golden Globe Awards in Beverly Hills.
48
2012
Kevin Mazur / Getty Images
The singer no doubt turned heads with her impressive Super Bowl performance outfits, including this gilded custom Givenchy number (by Riccardo Tisci).
49
2012
Kevin Mazur / Getty Images
Madonna enlisted Gaultier once again to design the costumes for her MDNA tour. Naturally, there was an updated cone bra, which is just as iconic as the original.
50
2012
Kevin Mazur / Getty Images
Her wardrobe for the MDNA tour also included this red and white cheerleader-inspired ensemble.
51
2013
Jamie McCarthy / Getty Images
Madonna worked with Tisci once again for this plaid outfit, which she wore for the punk-themed Met Gala in New York.
52
2014
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Madge took her son David Banda Mwale Ciccone Ritchie to the 56th Grammy Awards in Los Angeles, where they wore matching suits.
53
2015
Jason Merritt / Getty Images
The “Girl Gone Wild” singer unleashed her inner matador with this heavily embellished ensemble at the Grammys in LA. It was cheeky, to say the least.
54
2015
Kevork Djansezian / Getty Images
For her Grammys performance, Madonna stuck with the matador theme with this red number.
55
2015
Dimitrios Kambouris / Getty Images
For her Met Gala appearance, Madge rocked this black gown by designer Jeremy Scott.
56
2016
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Madonna’s bum made another red carpet appearance at the Met Gala, thanks to this sheer gown by Tisci for Givenchy.
57
2016
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The icon paid tribute to music legend Prince at the Billboard Music Awards. Fittingly, she wore a purple suit, inspired by the iconic one worn by the “Purple Rain” singer.
58
2017
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Never one to shy away from talking about politics, Madonna showed up at the Women’s March on Washington in 2017, wearing her own version of the popular pussy hat.
59
2017
John Shearer / Getty Images
For the Met Gala, Madonna wore another gown by Scott, this time in camo chic. She also appeared to be wearing a grill in her mouth.
60
2018
John Shearer / Getty Images
For this year’s Catholicism-themed Met Gala, Madonna wore another Gaultier gown. It didn’t involve a cone bra, but it definitely made a statement with its sheer cross cutout on the bodice.

CORRECTION: A previous version of this story included the wrong date for the photo of Madonna performing in a floral ensemble. It was 1987, not 1983.

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